Synthesis of branched allylic sulfones by regioselective boron-catalysed hydrosulfonylation

Branched allylic sulfones are scaffolds widely distributed in bioactive molecules and organic functional materials. The synthesis of allylic sulfones has been developed, e.g., using the Tsuji-Prost reaction, hydrosulfonylation and radical addition reactions, yet the hydrosulfonylation of unactive 1,...

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Published in:Environmental chemistry letters 2023-04, Vol.21 (2), p.681-687
Main Authors: Chang, Xiaoqiang, Chen, Xingyu, Zhang, Shuaichen, Lu, Sixian, Zhao, Yifan, Zhang, Dong, Yang, Lan, Ma, Yue, Sun, Peng
Format: Article
Language:English
Subjects:
Acids
Analytical Chemistry
Atom economy
Boron
Catalysts
Chemical synthesis
Earth and Environmental Science
Ecotoxicology
Environment
Environmental Chemistry
Functional materials
Geochemistry
Green chemistry
Inert atmospheres
Metals
Original Paper
Pollution
Regioselectivity
Sulfones
Transition metals
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Summary:Branched allylic sulfones are scaffolds widely distributed in bioactive molecules and organic functional materials. The synthesis of allylic sulfones has been developed, e.g., using the Tsuji-Prost reaction, hydrosulfonylation and radical addition reactions, yet the hydrosulfonylation of unactive 1,3-diene without transition metals has been rarely explored. Here we synthesized branched allylic sulfones by boron-catalysed highly regioselective hydrosulfonylation of 1,3-diene with sulfinic acid, without transition metal catalysts. Compared with the previous methods, the advantages include readily available starting materials without pre-treatment; cheap boron trifluoride etherate; simple operation and easy scaling-up; the reaction does not require dry conditions, an inert atmosphere or a water scavenger; and excellent atom economy and regioselectivity.
ISSN:1610-3653
1610-3661
DOI:10.1007/s10311-023-01570-w